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A Southernmost Road Trip: Delray Beach to Key West on the Overseas Highway

A day-long road-trip journey to Mile Marker 0 via the “The Highway That Goes to Sea,” shouldn’t be done without experiencing these amazing pit stops.


The Overseas Highway, the southernmost leg of U.S. Highway 1, isn’t just any old highway. Following a trail originally blazed in 1912 by Henry Flagler’s Florida East Coast Railroad, it’s a true modern wonder, stretching 113 miles – largely over water – from Miami to Key West. While you can drive the whole route in about three and half hours without stopping, it’s considered one of the most beautiful scenic drives in America, and, in order to fully enjoy it, it requires taking your time.

To make the most out of a day-long road trip crossing the countless coral and limestone islets down the full length of Florida Keys, rest up the night before in Delray Beach. Then come morning, hit the highway and stick pedal to the metal with no stops until you’re well past Miami. Then once you enter the Keys, be sure to hit these standout pit-stops along the mile markers (MM) before you arrive at your evening endpoint: Key West.

BEGIN | Depart from Delray Sands Resort [Delray Beach, FL]

Delray-Sand's-Latitudes

It will be tough to leave the ocean-inspired motifs, coral accents, and overarching retro-modern seaside vibe at this Highland Beach resort, but the Keys are a-calling. Still, before you go, fuel up with a breakfast of made-to-order omelets, fruit blintzes, croissants, and French toast at Latitudes. As the resort’s on-site restaurant, it’s as much a feast for the eyes as your appetite thanks to its immaculate atmosphere of light and bubble-themed décor.

MM 100 | Lunch at Skippers Dockside [Key Largo, FL]

After trudging through any traffic in Miami, it’ll likely be lunchtime, so make your first stop in the Upper Keys at this vintage boathouse-style restaurant that was formerly an ice house and a filling station. The outdoor tiki bar is perfectly situated to take in the gorgeous marina views while you watch passing fishing boats over a lunch menu of fresh-off-the-boat “soul food,” like lobster mac and cheese and coconut-crusted snapper.

MM 77.5 | Tarpon Feeding [Islamorada, FL]

Tarpon-Feeding-on-Islamorada

The biggest attraction at Robbie’s Marina – which is more like an eclectic tropical village, where you can rent boats, shop for art in the open-air market, and listen to live music – is, undoubtedly, the tarpon feeding. Daily, 100 or so tarpon come to the dock and linger for hours, and, for just a few bucks, you can hand-feed the large silver fish, who lack no fear of leaping out of the water to snatch a fish from your hand.

MM 48.5 | Turtle Hospital [Marathon, FL]

Is there anything sweeter than a hospital that rescues and rehabilitates sick and injured sea turtles? Housed in an old motel, this bright sea-green building has been converted to serve as living quarters for staff, so they are available 24/7 for their aquatic patients, as well as houses 23 individual tanks, ranging in size from 150 to 800 gallons. The largest tank of all is actually the former pool, holding up to 100,000 gallons of saltwater for these gentle swimmers.

MM 37 | Bahia Honda State Park [Big Pine Key, FL]

With soft white sands, azure waters, and palm trees, the beaches of Bahia Honda Key feel like they should be on a faraway Caribbean island instead of just off the Overseas Highway. In the heart of the Bahia Honda State Park, the mile-long Sandspur Beach is coveted for its shallow, calm waters (thanks to an offshore reef) and nearby park concession that operates daily hour-and-a-half snorkeling tours to the Looe Key National Marine Sanctuary.

MM 0 | Sunset at Opal Key Resort & Marina [Key West, FL]

Margaritaville's Bistro 245

Located right next to Mallory Square, the marina at this waterfront resort hub is famous for its daily evening celebration, offering – yes, a prime viewpoint of that amazing sunset – but also jugglers, island musicians, artists, and food vendors. Ready for dinner or a drink? Bistro 245, Opal Key Resort & Marina’s on-site restaurant, is the place to savor that same sunset view over a dish of truffle-crusted grouper from the comfortable outdoor dining area.

END | Check-in at Sunset Key Cottages

While most would say Key West is the end of the road, technically where you’ll be resting your head for the night is the true end. Located on a 27-acre private island, just an eight-minute ferry from Opal Key Resort’s marina, Sunset Key Cottages is the epitome of luxury and privacy with 40 stand-alone cottages all fully equipped with kitchens and private verandas. And, if looking to toast your trip after you’re arrival, look no further than a nightcap at Latitudes, the resort’s award-winning Key West restaurant, serving fresh flavorful island cuisine and hand-crafted cocktails made from local spirits like the restaurant’s own white or golden raw rum.

**Please confirm details with business/attractions prior to visiting due to possible restrictions.

Where to Stay

DELRAY BEACH, FL Opal Grand Oceanfront Resort & Spa | Delray Sands Resort

KEY WEST, FL Sunset Key Cottages | The Laureate Key WestOpal Key Resort & Marina | The Capitana Key West

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